Methanol → 6-(2-Bromoacetyl)-8-(tert-butyl)-3,4-dihydro-2H-1,4-benzoxazin-3-one

HRID 1296014Notes

Reaction equation

HRID 1296014 reaction equation
[Br-:1].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.[C:55]([C:58]1[CH:59]=[C:60]([C:69]([CH3:72])([CH3:71])[CH3:70])[C:61]2[O:66][CH2:65][C:64](=[O:67])[NH:63][C:62]=2[CH:68]=1)(=[O:57])[CH3:56].C(Cl)Cl.CO>C(Cl)(Cl)Cl>[Br:1][CH2:56][C:55]([C:58]1[CH:59]=[C:60]([C:69]([CH3:72])([CH3:71])[CH3:70])[C:61]2[O:66][CH2:65][C:64](=[O:67])[NH:63][C:62]=2[CH:68]=1)=[O:57]

Participants

6

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 229301966-acetyl-8-(tert-butyl)-3,4-dihydro-2H-1,4-benzoxazin-3-oneHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 229301756-(2-Bromoacetyl)-8-(tert-butyl)-3,4-dihydro-2H-1,4-benzoxazin-3-oneYield 92%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Tetra-n-butylammonium tribromide (64 mg, 0.13 mmol) was added to a solution of the 6-acetyl-8-(tert-butyl)-3,4-dihydro-2H-1,4-benzoxazin-3-one (30 mg, 0.12 mmol) in a methylene chloride (0.4 ml)-methanol (0.1 ml) mixed solvent under a nitrogen atmosphere, and the mixture was stirred at room temperature for 3 hours. After distilling off the solvent under reduced pressure, the residue was subjected to silica gel chromatography (Wakogel-C200,1 g) to yield the title compound (36 mg, 91% yield) as light yellow needle-like crystals from the chloroform fraction.

Workup

  1. additionmixed solvent under a nitrogen atmosphere
  2. distillationAfter distilling off the solvent under reduced pressure

Sources & evidence

ORD record
ord-ce8ae343bccf4cdab31b55eacc5fc5ed
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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